N-acylated methionine sulfoxides as food flavouring compounds

ABSTRACT

A flavour composition comprising a compound of formula (I) and edible salts thereof, wherein R 1  is an alkyl residue containing 2 to 18 carbon atoms, or an alkene residue containing from 9 to 25 carbon atoms with 1 to 6 double bonds, R 1  together with the carbonyl group to which it is attached is a residue of a carboxylic acid.

The present disclosure is concerned with certain carboxylic acid-aminoacid conjugates, flavour compositions containing said conjugates, andtheir use in edible compositions.

Many food flavour ingredients are known in the art that exert their ownvery pronounced flavour characteristics to a food product. Suchingredients may be of great value in niche areas for particular types offood categories, but can be incongruous, or even offensive, whenemployed in other food categories.

There is a need to provide broad spectrum flavour ingredients that actto complement or accentuate the taste and mouthfeel characteristics ofthe edible compositions into which they are incorporated.

The applicant has now found that a methionine sulfoxide connected to afatty acid residue through an amide bond may be employed as flavouringredients that complement or accentuate the taste and mouthfeelcharacteristics of edible compositions into which they are incorporatedacross a wide category of flavour applications.

The present disclosure provides in a first aspect compounds of formula(I)

their edible salts, and their use in edible compositions

wherein

R₁ is an alkyl residue containing 2 to 18 carbon atoms, or an alkeneresidue containing from 9 to 25 carbon atoms with 1 to 6 double bonds,R₁ together with the carbonyl group to which it is attached is a residueof a carboxylic acid.

Edible salts include those typically employed in the food and beverageindustry and include chlorides, sulphates, phosphates, gluconates,sodium, citrates, carbonates, acetates and lactates.

The carboxylic acids may be represented by abbreviations. Henceforth,the carboxylic acid residues may be referred to by the abbreviation Cn,wherein “n” represents the number of carbon atoms in the residue. Forexample, the residue of an 18 carbon acid may be abbreviated as C18.Still further, if the 18 carbon acid is saturated, e.g. stearic acid. Itmay be abbreviated as C18:0 (because it contains zero double bonds),whereas an 18 carbon acid having one double bond—e.g. oleic acid—may beabbreviated as C18:1. Still further, if the C18 acid has a single doublebond in the cis configuration, then it can be abbreviated as C18:1c.Similarly, if the double bond was in the trans configuration, then theabbreviation becomes C18:1t.

In a particular embodiment of the present disclosure the carboxylic acidresidue is a residue of a fatty acid.

The fatty acid residue may be the residue of a C2 to C18 fatty acid. Thefatty acid may be mammalian or non-mammalian. A mammalian fatty acid isa natural or synthetic fatty acid that is identical in structure to onenaturally produced in a mammal, including, but not limited to, myristicacid, palmitic acid, stearic acid, oleic acid, linoleic acid, linolenicacid, eicosatrienoic acid, arachidonic acid, eicosapentenoic acid, anddocosatetraenoic acid. A non-mammalian fatty acid is a natural orsynthetic fatty acid not normally produced by a mammal, including, butnot limited to, pentadecanoic acid; heptadecanoic acid; nonadecanoicacid; heneicosanoic acid; 9-trans-tetradecenoic acid;10-trans-pentadecenoic acid; 9-trans-hexadecenoic acid;10-trans-heptadecenoic acid; 10-trans-heptadecenoic acid;7-trans-nonadecenoic acid; 10,13-nonadecadienoic acid;11-trans-eicosenoic acid; and 12-transhenicosenoic acid.

The fatty acid residues may be saturated or unsaturated. In oneembodiment, if they are unsaturated, they have 1, 2 or 3 double bonds,which may be in cis- or trans-configuration.

In another embodiment, the fatty acid residues may be C16 to C18, andmay be saturated or unsaturated.

The skilled person will appreciate, however, that natural sources ofthese fatty acids, for example almond oil, avocado oil, castor oil,coconut oil, corn oil, cottonseed oil, olive oil, peanut oil, rice branoil, safflower oil, sesame oil, soybean oil, sunflower oil, palm oil andcanola oil, each consist of a complex mixture of fatty acids. Forexample, safflower oil is predominately a source of the C18:2 linoleicacid, nevertheless it may contain other fatty acids, such as linolenicacid (C18:3) and palmitic acid (C16:0), amongst others. Accordingly,reference herein to a compound containing a particular fatty acidresidue, for example a residue of C18 fatty acid, may be a reference toa pure, or substantially pure C18 fatty acid residue, or it may relateto a mixture of fatty acid residues with the predominant residue being aC18 residue. In one embodiment, fatty acid residues are C16 to C18.

The sulfoxide compounds of formula (I) can also be represented usingthese abbreviations. For example, the compound of formula (I) consistingof a residue of a C18 carboxylic acid and a Methionine sulfoxide(Met-SO) can be represented by the abbreviation C18-Met-SO. Forsimplicity the compounds of formula (I) henceforth may be represented inthis abbreviated form.

As is evident from the above formula (I), the amino nitrogen atom on theamino acid residue is bound to a carbonyl carbon atom of the carboxylicacid residue to form an amide linkage. Thus, the abbreviated formC18-Met-SO represents the compound of formula (I) in which theMethionine sulfoxide is connected via its nitrogen atom to the carbonylcarbon atom of a C18 carboxylic acid.

The compounds include C2-Met-SO, C6-Met-SO, C10-Met-SO, C12-Met-SO,C14-Met-SO, C15-Met-SO, C16-Met-SO, C17-Met-SO and C18-Met-SO.

The compounds include C2-Met-SO, C6-Met-SO, C10-Met-SO, C12-Met-SO,C14-Met-SO, C15-Met-SO, C16-Met-SO, C17-Met-SO and C18-Met-SO, whereinthe carboxylic acid residue is saturated.

The compounds include C2-Met-SO, C6-Met-SO, C10-Met-SO, C12-Met-SO,C14-Met-SO, C15-Met-SO, C16-Met-SO, C17-Met-SO and C18-Met-SO whereinthe carboxylic acid residue is unsaturated and contains 1, 2 or 3 doublebonds. The double bonds may be in cis-configuration, trans-configurationor a mixture of cis- and trans-configuration.

In one embodiment, the compounds bearing the Met-SO residue includeN-geranoyl-Met, N-palmitoyl-Met, N-palmitenoyl-Met, N-stearoyl-Met,N-linoleoyl-Met and N-linolenoyl-Met.

In one embodiment, sulfoxide compounds of formula (I) are selected fromthe group consisting of (2S)-2-acetamido-4-(methylsulfinyl)butanoicacid; (2S)-2-hexanamido-4-(methylsulfinyl)butanoic acid;(2S)-2-decanamido-4-(methylsulfinyl)butanoic acid;(2S)-2-((Z)-dodec-5-enamido)-4-(methylsulfinyl)butanoic acid;(2S)-2-dodecanamido-4-(methylsulfinyl)butanoic acid;(2S)-4-(methylsulfinyl)-2-tetradecanamidobutanoic acid;(2S)-4-(methylsulfinyl)-2-pentadecanamidobutanoic acid;(2S)-4-(methylsulfinyl)-2-palmitamidobutanoic acid;(2S)-2-heptadecanamido-4-(methylsulfinyl)butanoic acid;(2S)-4-(methylsulfinyl)-2-((9Z,12Z)-octadeca-9,12-dienamido)butanoicacid; (2S)-4-(methylsulfinyl)-2-oleamidobutanoic acid; and(2S)-4-(methylsulfinyl)-2-stearamidobutanoic acid.

The sulfoxide compounds of formula (I) can be formed by known methodsusing commercially available starting materials, reagents and solvents,and a detailed discussion is not warranted here. In one embodiment, theconjugates can be formed by the reaction of an amino acid with a fattyacid halide, e.g. a chloride under basic conditions in aqueousconditions such as a water/THF solvent system. Yield and reaction timesmay be improved by applying heat to the reaction mixture.

In yet another embodiment, an amino acid alkyl ester may be reacted witha fatty acid chloride under basic conditions in an aqueous-basedsolvent, such as a water/THF solvent system. Thereafter, the ester canbe hydrolysed carefully without affecting the amide bond in basicmethanol water solution

In yet another embodiment, a fatty acid and an amino acid alkyl estercan be reacted in dioxane in the presence of DCC(dicyclohexylcarbodiimide) and 1-hydroxypyrrolidine-2,5-dione. The estercan be hydrolysed carefully without affecting the amide bond in dilutebasic methanol water solution

In yet another embodiment, a (mixed) anhydride of a fatty acid isreacted with an amino acid in dioxane.

In yet another embodiment, a fatty acid alkyl ester can be reacted withan amino acid in dioxane

In still another embodiment, an amino acid alkyl ester is reacted with atriglyceride, optionally in the presence of a co-solvent. The amino acidester thus formed is then hydrolysed according to a method describedabove.

In yet another embodiment, an amino acid is reacted with a triglyceride,optionally in the presence of a co-solvent.

In yet another embodiment, an amino acid is reacted with a triglyceridein the presence of a lipase, esterase, peptidase, amidase or acylase,optionally in the presence of a cosolvent and/or water.

In yet another embodiment a fatty acid alkyl ester is reacted with anamino acid in the presence of a lipase or an acylase, optionally in thepresence of a co-solvent and/or water.

The sulfoxide compounds of formula (I) impart remarkable organolepticproperties to edible compositions to which they are added. Inparticular, they impart highly intense, authentic and harmoniousflavour, and a roundness and fullness to edible compositions containingthem.

More particularly, the compounds can be incorporated into an edibleproduct to impart a remarkable mouthfeel, body and enhanced fatperception; or an enhanced umami or salt taste. They are particularlyuseful in applications low in fat, salt and umami.

This finding was all the more surprising considering that when applicanttasted the compounds in dilute aqueous solution, they were eithertasteless or they exhibited a disappointing, faintly fatty tasteprofile. As such, they appeared to be quite unsuitable for use inflavour applications. Only their combination with flavour co-ingredientsand the judicious selection of their usage levels was it possible todiscover the remarkable organoleptic properties of these compounds.Their effect on edible compositions is quite unusual in that rather thanexerting a characteristic flavour profile to a foodstuff or a beverage,they actually complement, lift or accentuate the essential or authenticflavour and mouth feel characteristics of the foods or beverages inwhich they are incorporated. Accordingly, the compounds of the presentdisclosure find utility in a broad spectrum of applications in the foodand beverage industry, as well as in health and wellness.

Accordingly, in one embodiment, a method of conferring flavour and/ormouthfeel to, or improving taste and/or mouthfeel of an ediblecomposition, which method comprises adding to said composition asulfoxide compound of formula (I) defined herein.

The remarkable organoleptic effects are observed when the sulfoxidecompounds of formula (I) are incorporated into an edible compositioncontaining one or more flavour co-ingredients.

The flavour co-ingredients may be sugars, fats, salt (e.g. sodiumchloride), MSG, calcium ions, phosphate ions, organic acids, proteins,purines and mixtures thereof

In a particular embodiment, sugars are present in amounts of 0.001% to90%, more particularly 0.001% to 50%, still more particularly 0.001% to20% based on the total weight of an edible composition.

In a particular embodiment, fats are present in amounts of 0.001% to100%, more particularly 0.001% to 80%, more particularly 0.001% to 30%,still more particularly 0.001% to 5% based on the total weight of anedible composition.

In a particular embodiment, salt (e.g. sodium chloride) is present inamounts of 0.001% to 20%, more particularly 0.001% to 5% based on thetotal weight of an edible composition.

In a particular embodiment, MSG is present in amounts of 0.001% to 2%based on the total weight of an edible composition.

In a particular embodiment, calcium is present in amounts of 0.001% to50% more particularly 0.001% to 20%, still more particularly 0.001% to1% based on the total weight of an edible composition.

In a particular embodiment, organic acids are present in amounts of0.001% to 10%, more particularly 0.001% to 7% based on the total weightof an edible composition.

Types of organic acids include citric, malic, tartaric, fumaric, lactic,acetic, succinic. Types of edible compositions containing organic acidsinclude beverages, such as carbonated soft drink beverages, stillbeverages, juices, powdered soft drinks, liquid concentrates, alcoholicbeverages and functional beverages.

In a particular embodiment, phosphorus is present in an amount up to0.5% by weight of an edible composition. Typically phosphorus is presentas a phosphate or phosphoric acid.

In a particular embodiment, purines are present in an amount up to 0.5%by weight of an edible composition. The term “purines” includeribonucleotides such as IMP and GMP.

Despite their interesting organoleptic properties, nevertheless,applicant found that formulating the sulfoxide compounds of formula (I)was not a trivial matter. The discovered potency of the compoundssuggested that they could be employed at very low levels in flavourapplications, and so for ease of handling, mixing and processing withother ingredients, although it is possible to use the compounds in neatform, it is desirable to extend or add volume to the physical form ofthe compounds by incorporating them into a suitable vehicle, for examplea diluent, such as a solvent. However, the compounds are solids orviscous oils at ambient temperatures, and have very limited solubilityin water. Applicant found that an at least about 0.01% stock solution,more particularly about 0.01-1% stock solution of a sulfoxide compoundof formula (I) achieved a balance regarding acceptable solvent levelsfor ease of handling and mixing, and the desire to limit the amount ofsolvent that would have to be removed from the stock solution whenfurther processing of the compounds in flavour compositions and edibleproducts for reasons of palatability, efficiency, cost and the like.Applicant found that suitable solvents for the stock solution includeethanol, triacetine, glycerol and miglyol.

In order to aid in the process of solubilization and produce a stocksolution and minimize the amount of solvent, sulfoxide compounds of theformula (I) formed from a mixture of carboxylic acids, rather than apure carboxylic acid may be used.

Accordingly, there is provided in another aspect of the presentdisclosure an at least about 0.01% stock solution, more particularlyabout 0.01-1% stock solution of a sulfoxide compound of formula (I).

The stock solution may contain other materials such as carrier materialsand/or adjuvants more fully described below. In a particular embodiment,the stock solution contains an anti-oxidant selected from the groupconsisting of vitamin C, vitamin E, rosemary extract, antrancine,butylated hydroxyanisole (BHA) and butylated hydroxytoluene (BHT).Anti-oxidants are preferably employed to prevent, or significantlyreduce, generation of volatile off notes as a result of degradation ofthe compounds of formula (I). In one example, anti-oxidants are usedwhen the compounds of formula (I) bear a residue of an unsaturated fattyacid. In another embodiment, anti-oxidants are used if the fatty acidresidue contains more than 1 double bond. Determination of an effectiveamount of anti-oxidant is within the purview of the skilled person,however amounts in the range of about 10 ppm to 1000 ppm based on theweight of the stock solution may be present.

In preparing the flavour compositions in accordance with the presentdisclosure, the sulfoxide compounds of formula (I) may be employed inany physical form. They may be used in neat form, in the form of a stocksolution described above; they may be used in the form of an emulsion;or they may be used in a powder form. If the sulfoxide compounds offormula (I) are presented in the form of a powder, the powder form canbe produced by a dispersive evaporation process, such as a spray dryingprocess as is more fully described below. The powder form may beprepared by subjecting a liquid formulation containing a sulfoxidecompound of formula (I) to a dispersive evaporation process. The liquidformulation may comprise a solution, suspension or emulsion comprisingthe sulfoxide compound of formula (I). In particular, the liquidformulation may take the form of the stock solution describedhereinabove. The liquid formulation may contain other ingredients suchas a carrier material and/or an adjuvant as described more fully below.

A powder comprising a sulfoxide compound of formula (I) forms anotheraspect of the present disclosure.

The sulfoxide compounds of formula (I) may in incorporated into anedible composition alone, or in the form of a flavour compositioncomprising one or more flavour co-ingredients.

A flavour composition comprising a sulfoxide compound according to theformula (I) forms another aspect of the present disclosure.

In an embodiment, the flavour formulation comprises a sulfoxide compoundof formula (I) and at least flavour co-ingredient.

In a particular embodiment, the flavour composition comprises:

-   -   i) a sulfoxide compound according to formula (I);    -   ii) at least one flavour co-ingredient;    -   iii) optionally a carrier material; and    -   iv) optionally at least one adjuvant.

By the term “flavour co-ingredient” is an ingredient that is able tocontribute or impart or modify in a positive or pleasant way the tasteof an edible composition.

All manner of flavour co-ingredients may be employed in a compositionaccording to the present disclosure, including, but not limited to,natural flavours, artificial flavours, spices, seasonings, and the like.Flavour co-ingredients include synthetic flavour oils and flavouringaromatics and/or oils, oleoresins, essences, distillates, and extractsderived from plants, leaves, flowers, fruits, and so forth, andcombinations comprising at least one of the foregoing.

Flavour oils include spearmint oil, cinnamon oil, oil of wintergreen(methyl salicylate), peppermint oil, Japanese mint oil, clove oil, bayoil, anise oil, eucalyptus oil, thyme oil, cedar leaf oil, oil ofnutmeg, allspice, oil of sage, mace, oil of bitter almonds, and cassiaoil; useful flavouring agents include artificial, natural and syntheticfruit flavours such as vanilla, and citrus oils including lemon, orange,lime, grapefruit, yazu, sudachi, and fruit essences including apple,pear, peach, grape, blueberry, strawberry, raspberry, cherry, plum,prune, raisin, cola, guarana, neroli, pineapple, apricot, banana, melon,apricot, ume, cherry, raspberry, blackberry, tropical fruit, mango,mangosteen, pomegranate, papaya and the like.

Additional exemplary flavours imparted by a flavouring agent include amilk flavour, a butter flavour, a cheese flavour, a cream flavour, and ayogurt flavour; a vanilla flavour; tea or coffee flavours, such as agreen tea flavour, an oolong tea flavour, a tea flavour, a cocoaflavour, a chocolate flavour, and a coffee flavour; mint flavours, suchas a peppermint flavour, a spearmint flavour, and a Japanese mintflavour; spicy flavours, such as an asafetida flavour, an ajowanflavour, an anise flavour, an angelica flavour, a fennel flavour, anallspice flavour, a cinnamon flavour, a chamomile flavour, a mustardflavour, a cardamom flavour, a caraway flavour, a cumin flavour, a cloveflavour, a pepper flavour, a coriander flavour, a sassafras flavour, asavoury flavour, a Zanthoxyli Fructus flavour, a perilla flavour, ajuniper berry flavour, a ginger flavour, a star anise flavour, ahorseradish flavour, a thyme flavour, a tarragon flavour, a dillflavour, a capsicum flavour, a nutmeg flavour, a basil flavour, amarjoram flavour, a rosemary flavour, a bayleaf flavour, and a wasabi(Japanese horseradish) flavour; a nut flavour such as an almond flavour,a hazelnut flavour, a macadamia nut flavour, a peanut flavour, a pecanflavour, a pistachio flavour, and a walnut flavour; alcoholic flavours,such as a wine flavour, a whisky flavour, a brandy flavour, a rumflavour, a gin flavour, and a liqueur flavour; floral flavours; andvegetable flavours, such as an onion flavour, a garlic flavour, acabbage flavour, a carrot flavour, a celery flavour, mushroom flavour,and a tomato flavour.

In some embodiments, said flavour co-ingredients include aldehydes andesters such as cinnamyl acetate, cinnamaldehyde, citral diethylacetal,dihydrocarvyl acetate, eugenyl 49 formate, p-methylamisol, and so forthcan be used. Further examples of aldehyde flavourings includeacetaldehyde (apple), benzaldehyde (cherry, almond), anisic aldehyde(licorice, anise), cinnamic aldehyde (cinnamon), citral, i.e.,alpha-citral (lemon, lime), neral, i.e., beta-citral (lemon, lime),decanal (orange, lemon), ethyl vanillin (vanilla, cream), heliotrope,i.e., piperonal (vanilla, cream), vanillin (vanilla, cream), alpha-amylcinnamaldehyde (spicy fruity flavours), butyraldehyde (butter, cheese),valeraldehyde (butter, cheese), citronellal (modifies, many types),decanal (citrus fruits), aldehyde C-8 (citrus fruits), aldehyde C-9(citrus fruits), aldehyde C-12 (citrus fruits), 2-ethyl butyraldehyde(berry fruits), hexenal, i.e., trans-2 (berry fruits), tolyl aldehyde(cherry, almond), veratraldehyde (vanilla), 2,6-dimethyl-5-heptenal,i.e., melonal (melon), 2,6-dimethyloctanal (green fruit), and2-dodecenal (citrus, mandarin), and the like.

Further examples of other flavour co-ingredients can be found in“Chemicals Used in Food Processing”, publication 1274, pages 63-258, bythe National Academy of Sciences.

In particular embodiments, the flavour co-ingredient is selected fromthe compounds and compositions disclosed in WO2005102701, WO2006009425,WO2005096843, WO2006046853 and WO2005096844, all of which references areherein incorporated by reference in their entirety.

Flavour co-ingredients may include known salt tastants, umami tastants,and savoury flavour compounds. Non limiting examples include: NaCl, KCl,MSG, guanosine monophosphate (GMP), inosin monophospahte (IMP),ribonucleotides such as disodium inosinate, disodium guanylate,N-(2-hydroxyethyl)-lactamide, N-lactoyl-GMP, N-lactoyl tyramine, gammaamino butyric acid, allyl cysteine,1-(2-hydroxy-4-methoxylphenyl)-3-(pyridine-2-yl)propan-1-one, arginine,potassium chloride, ammonium chloride, succinic acid,N-(2-methoxy-4-methyl benzyl)-N′-(2-(pyridin-2-yl)ethyl) oxalamide,N-(heptan-4-yl)benzo(D)(1,3)dioxole-5-carboxamide,N-(2,4-dimethoxybenzyl)-N′-(2-(pyridin-2-yl)ethyl) oxalamide,N-(2-methoxy-4-methyl benzyl)-N′-2(2-(5-methyl pyridin-2-yl)ethyl)oxalamide, cyclopropyl-E,Z-2,6-nonadienamide.

The carrier material may be employed in compositions according to thepresent disclosure to encapsulate or to entrap in a matrix the othercomponents of the composition. The role of the carrier material may bemerely that of a processing aid or a bulking agent, or it might beemployed to shield or protect the other components from the effects ofmoisture or oxygen or any other aggressive media. The carrier materialmight also act as a means of controlling the release of flavour fromedible compositions.

Carrier materials may include mono, di- or trisaccharides, natural ormodified starches, hydrocolloids, cellulose derivatives, polyvinylacetates, polyvinylalcohols, proteins or pectins. Example of particularcarrier materials include sucrose, glucose, lactose, levulose, fructose,maltose, ribose, dextrose, isomalt, sorbitol, mannitol, xylitol,lactitol, maltitol, pentatol, arabinose, pentose, xylose, galactose,maltodextrin, dextrin, chemically modified starch, hydrogenated starchhydrolysate, succinylated or hydrolysed starch, agar, carrageenan, gumarabic, gum accacia, tragacanth, alginates, methyl cellulose,carboxymethyl cellulose, hydroxyethyl cellulose, hydroxypropylmethylcellulose, derivatives and mixtures thereof. Of course, one skilled inthe art will appreciate that the cited materials are hereby given by wayof example and are not to be interpreted as limiting the present subjectmatter.

By “flavour adjuvant” is meant an ingredient capable of impartingadditional added benefit to compositions of the present disclosure suchas a colour, light resistance, chemical stability and the like. Suitableadjuvants include solvents (including water, alcohol, ethanol,triacetine, oils, fats, vegetable oil and miglyol), binders, diluents,disintegrating agents, lubricants, colouring agents, preservatives,antioxidants, emulsifiers, stabilisers, anti-caking agents, and thelike. In a particular embodiment, the flavour composition comprises ananti-oxidant. Said anti-oxidants may include vitamin C, vitamin E,rosemary extract, antrancine, butylated hydroxyanisole (BHA) andbutylated hydroxytoluene (BHT).

Examples of such carriers or adjuvants for flavour compositions may befound in for example, “Perfume and Flavour Materials of Natural Origin”,S. Arctander, Ed., Elizabeth, N.J., 1960; in “Perfume and FlavourChemicals”, S. Arctander, Ed., Vol. I & II, Allured PublishingCorporation, Carol Stream, USA, 1994; in “Flavourings”, E. Ziegler andH. Ziegler (ed.), Wiley-VCH Weinheim, 1998, and “CTFA CosmeticIngredient Handbook”, J. M. Nikitakis (ed.), 1st ed., The Cosmetic,Toiletry and Fragrance Association, Inc., Washington, 1988.

Other suitable and desirable ingredients of flavour compositions aredescribed in standard texts, such as “Handbook of Industrial ChemicalAdditives”, ed. M. and I. Ash, 2^(nd) Ed., (Synapse 2000).

Flavour compositions according to the present disclosure may be providedin any suitable physical form. For example, they may be in the form ofoils, emulsions or dispersions in a hydrous liquid or organic liquidsuitable for use in edible compositions, or solid form, such as powders.

If the flavour compositions are to be provided in the form of a powderedcomposition, they may be prepared by dispersive evaporation techniquesgenerally known in the art, such as spray drying.

Accordingly, in another aspect, there is provided a method of forming apowder composition, comprising the steps of providing a liquidcomposition comprising a sulfoxide compound of the formula (I) and oneor more optional ingredients selected from at least one flavourco-ingredient, a carrier material and an adjuvant, and dispersivelyevaporating said liquid composition to form a powder composition.

In this manner, a sulfoxide compound of formula (I) or a flavourcomposition comprising said compound may be presented in a powder form.

The liquid composition used in the preparation of a powder may be in theform of a solution, emulsion, dispersion or slurry. The liquid maycontain water, and/or an organic liquid, such as ethanol, glycerol,triacetine, miglyol (MCT) that is acceptable for use in ediblecompositions.

In another embodiment, powder compositions may be prepared according tomethods and apparatus known in the art for producing powders on anindustrial scale. A particularly suitable method is spray drying. Spraydrying techniques and apparatus are well known in the art and need nodetailed discussion herein. The spray drying techniques, apparatus andmethods described in US2005/0031769 and US2013/0022728, as well as thosetechniques, apparatus and methods described in those documents aresuitable for producing powder compositions of the present disclosure andare herein incorporated by reference in their entirety.

The manner in which the sulfoxide compounds of formula (I) areincorporated into powder flavour compositions is not critical. Forexample, the compounds may be added to the liquid composition describedabove and be subjected to a dispersive evaporation process along withall the other components of the flavour composition. Alternatively,compounds may be added to the flavour composition after it has beenformed as a powder.

Many of the flavour co-ingredients described herein above are volatileand/or may be sensitive to oxidative degradation, particularly whensubjected to elevated temperature, and under humid conditions.Accordingly, particular problems can arise when subjecting flavourco-ingredients described above to dispersive evaporation processes suchas spray drying. A non-exhaustive list of ingredients that can beparticularly susceptible include, those ingredients containingartificial, natural or synthetic fruit flavours such as vanilla,chocolate, coffee, cocoa and citrus oil, including lemon, orange, grape,lime and grapefruit, and fruit essences including apple, pear, peach,strawberry, raspberry, cherry, plum, pineapple, apricot and the like.The volatile components of these flavour co-ingredients may include, butare not limited to, acetaldehyde, dimethyl sulfide, ethyl acetate, ethylpropionate, methyl butyrate, and ethyl butyrate. Flavour co-ingredientscontaining volatile aldehydes or esters include, e.g., cinnamyl acetate,cinnamaldehyde, citral, diethylacetal, dihydrocarvyl acetate, eugenylformate, and p-methylanisole. Further examples of volatile compoundsthat may be present as co-ingredients include acetaldehyde (apple);benzaldehyde (cherry, almond); cinnamic aldehyde (cinnamon); citral,i.e., alpha citral (lemon, lime); neral, i.e., beta citral (lemon,lime); decanal (orange, lemon); ethyl vanillin (vanilla, cream);heliotropine, i.e., piperonal (vanilla, cream); vanillin (vanilla,cream); alpha-amyl cinnamaldehyde (spicy fruity flavors); butyraldehyde(butter, cheese); valeraldehyde (butter, cheese); citronellal (modifies,many types); decanal (citrus fruits); aldehyde C-8 (citrus fruits);aldehyde C-9 (citrus fruits); aldehyde C-12 (citrus fruits); 2-ethylbutyraldehyde (berry fruits); hexenal, i.e., trans-2 (berry fruits);tolyl aldehyde (cherry, almond); veratraldehyde (vanilla);2,6-dimethyl-5-heptenal, i.e., melonal (melon); 2-6-dimethyloctanal(green fruit); and 2-dodecenal (citrus, mandarin); cherry; or grape andmixtures thereof.

Applicant surprisingly found that the inclusion of a sulfoxide compoundof formula (I) in a powder flavour composition, it was possible tomaintain the flavour quality of flavour composition converted intopowdered form by a dispersive evaporation process.

Accordingly, there is provided in another aspect of the presentdisclosure a method of maintaining flavour quality of a powder flavourcomposition comprising the step of including in said powder flavourcomposition a sulfoxide compound of formula (I).

As stated hereinabove, compounds of formula (I) or flavour compositionscontaining such sulfoxide compounds can be incorporated into ediblecompositions, and an edible composition containing such a compound orflavour composition forms another aspect of the present disclosure.

The term “edible composition” refers to products for consumption by asubject, typically via the oral cavity (although consumption may occurvia non-oral means such as inhalation), for at least one of the purposesof enjoyment, nourishment, or health and wellness benefits. Ediblecompositions may be present in any form including, but not limited to,liquids, solids, semi-solids, tablets, capsules, lozenges, strips,powders, gels, gums, pastes, slurries, syrups, aerosols and sprays. Theterm also refers to, for example, dietary and nutritional supplements.Edible compositions include compositions that are placed within the oralcavity for a period of time before being discarded but not swallowed. Itmay be placed in the mouth before being consumed, or it may be held inthe mouth for a period of time before being discarded. An ediblecomposition as herein above defined includes compositions whose taste ismodified in the manner described herein by the addition of sulfoxidecompounds of formula (I) or whose taste is so modified by processingsuch that it is enriched in a sulfoxide compound of formula (I).

In a particular embodiment the term “edible compositions” refers toproducts for consumption by a subject, typically via the oral cavity(although consumption may occur via non-oral means such as inhalation),for one of the purposes of enjoyment or nourishment.

In a more particular embodiment the term “edible compositions” refers toproducts for consumption by a subject, typically via the oral cavity(although consumption may occur via non-oral means such as inhalation),for the purpose of enjoyment. Still more particularly, the term refersto foodstuffs and beverages.

In a particular embodiment, the term “edible composition” does notrelate to pharmaceutical compositions.

In another embodiment, the term “edible composition” does not relate tonutritional supplements.

Broadly, the edible composition includes, but is not limited tofoodstuffs of all kinds, confectionery products, baked products, sweetproducts, savoury products, fermented products, dairy products,beverages and oral care products.

Exemplary foodstuffs include, but are not limited to, chilled snacks,sweet and savoury snacks, fruit snacks, chips/crisps, extruded snacks,tortilla/corn chips, popcorn, pretzels, nuts, other sweet and savourysnacks, snack bars, granola bars, breakfast bars, energy bars, fruitbars, other snack bars, meal replacement products, slimming products,convalescence drinks, ready meals, canned ready meals, frozen readymeals, dried ready meals, chilled ready meals, dinner mixes, frozenpizza, chilled pizza, soup, canned soup, dehydrated soup, instant soup,chilled soup, uht soup, frozen soup, pasta, canned pasta, dried pasta,chilled/fresh pasta, noodles, plain noodles, instant noodles, cups/bowlinstant noodles, pouch instant noodles, chilled noodles, snack noodles,dried food, dessert mixes, sauces, dressings and condiments, herbs andspices, spreads, jams and preserves, honey, chocolate spreads, nut-basedspreads, and yeast-based spreads.

Exemplary confectionery products include, but are not limited to,chewing gum (which includes sugarized gum, sugar-free gum, functionalgum and bubble gum), centerfill confections, chocolate and otherchocolate confectionery, medicated confectionery, lozenges, tablets,pastilles, mints, standard mints, power mints, chewy candies, hardcandies, boiled candies, breath and other oral care films or strips,candy canes, lollipops, gummies, jellies, fudge, caramel, hard and softpanned goods, toffee, taffy, liquorice, gelatin candies, gum drops,jelly beans, nougats, fondants, combinations of one or more of theabove, and edible flavour compositions incorporating one or more of theabove.

Exemplary baked products include, but are not limited to, alfajores,bread, packaged/industrial bread, unpackaged/artisanal bread, pastries,cakes, packaged/industrial cakes, unpackaged/artisanal cakes, cookies,chocolate coated biscuits, sandwich biscuits, filled biscuits, savourybiscuits and crackers, bread substitutes,

Exemplary sweet products include, but are not limited to, breakfastcereals, ready-to-eat (“rte”) cereals, family breakfast cereals, flakes,muesli, other ready to eat cereals, children's breakfast cereals, hotcereals,

Exemplary savoury products include, but are not limited to, salty snacks(potato chips, crisps, nuts, tortilla-tostada, pretzels, cheese snacks,corn snacks, potato-snacks, ready-to-eat popcorn, microwaveable popcorn,pork rinds, nuts, crackers, cracker snacks, breakfast cereals, meats,aspic, cured meats (ham, bacon), luncheon/breakfast meats (hotdogs, coldcuts, sausage), tomato products, margarine, peanut butter, soup (clear,canned, cream, instant, UHT), canned vegetables, pasta sauces.

Exemplary dairy products include, but are not limited to, cheese, cheesesauces, cheese-based products, ice cream, impulse ice cream, singleportion dairy ice cream, single portion water ice cream, multi-packdairy ice cream, multi-pack water ice cream, take-home ice cream,take-home dairy ice cream, ice cream desserts, bulk ice cream, take-homewater ice cream, frozen yoghurt, artisanal ice cream, dairy products,milk, fresh/pasteurized milk, full fat fresh/pasteurized milk, semiskimmed fresh/pasteurized milk, long-life/uht milk, full fat longlife/uht milk, semi skimmed long life/uht milk, fat-free long life/uhtmilk, goat milk, condensed/evaporated milk, plain condensed/evaporatedmilk, flavoured, functional and other condensed milk, flavoured milkdrinks, dairy only flavoured milk drinks, flavoured milk drinks withfruit juice, soy milk, sour milk drinks, fermented dairy drinks, coffeewhiteners, powder milk, flavoured powder milk drinks, cream, yoghurt,plain/natural yoghurt, flavoured yoghurt, fruited yoghurt, probioticyoghurt, drinking yoghurt, regular drinking yoghurt, probiotic drinkingyoghurt, chilled and shelf-stable desserts, dairy-based desserts,soy-based desserts.

Exemplary beverages include, but are not limited to, flavoured water,soft drinks, fruit drinks, coffee-based drinks, tea-based drinks,juice-based drinks (includes fruit and vegetable), milk-based drinks,gel drinks, carbonated or non-carbonated drinks, powdered drinks,alcoholic or non-alcoholic drinks

Exemplary fermented foods include, but are not limited to, cheese andcheese products, meat and meat products, soy and soy products, fish andfish products, grain and grain products, fruit and fruit products.

In a particular embodiment the consumable product is selected from thegroup consisting of soy sauce, cheese, soup, hot and cold sauces,fruits, vegetables, ketchups, tea, coffee, snacks such as potato chipsor extruded snacks.

The sulfoxide compounds of formula (I), when added to a flavourcomposition and/or an edible composition act on the composition tocomplement its flavour and/or mouthfeel to render it more delicious andauthentic. The effects may be temporal or related to intensity, forexample the compounds may act by enhancing, strengthening, softening,sharpening a flavour, or making more salivating. The sulfoxide compoundsof formula (I) may also affect the temporal profile of a flavour, thatis, they may affect the initial impact of a flavour, the body of aflavour, or its lingering effect.

The sulfoxide compounds of formula (I) may modify any aspect of thetemporal profile of taste or flavour of an edible composition. Inparticular, the compounds improve mouthfeel and impart more creamy andfatty sensations.

Sulfoxide compounds of formula (I) or flavour compositions containingsame may be added to edible compositions in widely varying amounts. Theamount will depend on the nature of the edible composition to beflavoured, and on the desired effect, as well as on the nature of theingredients present in said flavour composition. In order to obtain theremarkable beneficial effects attributed to the presence of thesulfoxide compounds of formula (I), the flavour composition should beemployed in amounts such that the sulfoxide compounds of formula (I) arepresent in amounts of 1 part per billion to 10 parts per million basedon the total weight of the edible composition. Whereas amounts higherthan this can be employed, the beneficial effects are considerably lessapparent and undesirable off-notes can become increasingly apparent.

Interesting organoleptic effects, e.g. salt, alcohol or coolant boostingeffects, in edible compositions containing salt or alcohol or coolantcompounds can be achieved when sulfoxide compounds of the formula (I)are employed at levels of 1 to 100 ppb.

Interesting organoleptic effects, for example umami boosting effects, inedible compositions containing umami tastants can be achieved whensulfoxide compounds of the formula (I) are employed at levels of 100 to250 ppb.

Interesting organoleptic effects, in particular mouthfeel boostingeffects, in edible compositions can be achieved when sulfoxide compoundsof the formula (I) are employed at levels of 250 to 500 ppb.

Interesting organoleptic effects, e.g. fat boosting effects, in ediblecompositions containing fats can be achieved when sulfoxide compounds ofthe formula (I) are employed at levels of 500 to 1000 ppb.

It is particularly advantageous to incorporate sulfoxide compounds offormula (I) into edible compositions that are formed under conditions ofhigh temperature, such as baking, frying or which are processed by heattreatments such as pasteurization or under UHT conditions. Under highpreparation or processing temperatures, volatile flavour ingredients maybe lost or degraded with the result that flavour intensity can bereduced and the essential and authentic flavour characteristics can bediminished. Such edible products include dairy products, snack foods,baked products, powdered soft drinks and similar dry mixes, and thelike, fats and condiments, mayonnaise, dressings, soups and bouillons,and beverages.

In another embodiment, edible compositions according to the presentdisclosure are powdered soft drinks and similar dry mix applications.Dry mix applications are known in the art and included products inpowder form that are intended to be reconstituted before consumption.They include powdered soups, powdered cake mixes, powdered chocolatedrinks, instant coffees, seasonings and fonds, and the like.

Dry powders formed by dispersive evaporation processes, such as spraydrying, represent a very convenient vehicle to deliver flavour oilquality flavours to edible compositions.

Unfortunately, flavour oils, and in particular citrus flavour oils canbe particularly sensitive to dispersive evaporation processes,especially processes carried out at high temperature. Flavour oils tendto evaporate or degrade to form products having unfavourable off-notes.Powdered flavour compositions, particularly those containing citrusoils, can be of poor quality and exhibit relatively short self-life, asa result.

Surprisingly, the incorporation of sulfoxide compounds of formula (I) orflavour compositions containing same into powder compositions, resultsin powder compositions that exhibit the impact and authenticity of theflavour oils used in their preparation, essentially maintaining flavouroil quality in a powdered flavour formulations.

Accordingly, in another aspect a powder flavour composition comprising asulfoxide compound according to formula (I) and at least one additionalflavour co-ingredient is provided.

In another aspect of the present disclosure there is provided a powdersoft drink composition or other dry mix composition comprising asulfoxide compound according to formula (I).

In yet another aspect of the present disclosure there is provided apowder soft drink composition or other dry mix composition comprising apowder flavour composition comprising a sulfoxide compound of formula(I).

In yet another aspect, there is provided a method of forming a powderflavour composition comprising the step of incorporating into saidcomposition a sulfoxide compound according to formula (I).

In one embodiment, the sulfoxide compound of formula (I) may be added tothe formed powder flavour composition, or it may be added to flavourcomposition before forming the powder.

In another embodiment, snack foods are a class of edible compositionaccording to the present disclosure. Snack foods are a category ofproduct well known to the skilled person in the food industry. Theseproducts are described above and include, without limitation, pretzels,corn chips, potato chips, puffed products, extruded products, tortillachips and the like. Still more particularly, the present disclosure isconcerned with low fat snack food compositions. Low fat snack foodcompositions contain less than 30% by weight fat, more particularlybetween 5 to 25% by weight of fat.

A problem with reducing fat in a snack food composition is the loss intaste and texture. Fats play an important role in the way that doughbehaves during processing and greatly affect the quality, flavor andtexture of ready-to-eat products. As the fat content in snack productsis reduced or replaced with other ingredients (e.g., non-digestible fat,protein, fiber, gums), adverse organoleptic effects (e.g., mouthcoating, drying, lack of crispness and lack of flavour) are increased.The adverse organoleptic effects result in products having reducedpalatability.

Considerable efforts have been expended in devising flavour compositionsto overcome the problems associated with low fat snack food products.Flavours may be applied to a snack food as topical coatings in the formof dry powders and/or as liquids (e.g., oil-based, water-based). Anotherapproach has been to add flavour to the dough.

Despite these various approaches which have been taken to improveconsumer appeal and palatability of snack foods, and particularly lowfat snack foods, there is still a need for improved low-fat snack foodshaving coatings applied thereto with the visual appeal, flavor, andtexture of full-fat snack foods.

Sulfoxide compounds according to formula (I) or flavour compositionscontaining same can be incorporated into snack foods to impart animpactful flavour and a mouthfeel with a remarkable roundness andfullness. Furthermore, the taste and mouthfeel effects can be achievedeven in low fat snack foods.

Accordingly, the present disclosure provides in another of its aspects asnack food comprising a flavour composition as hereinabove described. Inone embodiment, the snack food has a fat content of about 40% or less byweight based on the total weight of the snack food, more particularlyabout 30% or less, still more particularly 25% or less, moreparticularly still about 10% or less, still more particularly about 5%or less, still more particularly about 3% or less.

Examples of snack foods are described above and include productsprocessed by oven baking, extrusion or frying, and which are made frompotato and/or corn and/or various grains such as rice or wheat.

Another particularly preferred class of edible composition according tothe present disclosure is alcoholic beverages.

Applicant surprisingly found that compounds according to formula (I)incorporated into an alcoholic beverage had the effect of increasing thealcohol impact of the beverage.

Accordingly, there is provided in another aspect of the presentdisclosure an alcoholic beverage comprising a compound according toformula (I).

In yet another aspect of the present disclosure there is provided amethod of producing a heightened alcoholic impression in an alcoholicbeverage by incorporating into said beverage a compound according toformula (I).

Compounds of formula (I) may be incorporated into said alcoholicbeverage in amounts of 1 ppb to 1 ppm.

Another preferred class of edible compositions are products ingested inthe form of tablets, capsules, powders, multiparticulates and the like,which may include pharmaceuticals and nutraceuticals.

Certain groups of people have problems swallowing tablets or capsules,powders, multi-particulates and the like. This problem can beparticularly pronounced in certain consumer groups, such as children andthe very old or infirm. Applicant surprisingly found that compoundsaccording to the formula (I) when taken into the oral cavity produce apronounced salivating effect. Incorporating the compounds into thesedosage forms, particularly as part of a coating around said dosage formscan ease the swallowing process for consumers, in particular childrenand the old or infirm.

Accordingly, there is provided in another aspect of the presentdisclosure an orally administrable dosage form, in particular in theform of tablets capsules, powders or multiparticulates comprising acompound according to the formula (I).

Another preferred class of edible composition is baked goods. Compoundsof the formula (I) may be incorporated topically or in-dough.Incorporated at levels of 1 ppb to 1 ppm, the compounds of formula (I)render baked products less dry and more succulent.

Other preferred class of edible compositions are caloric or non-caloricbeverages containing carbohydrate sweeteners, such as sucrose, highfructose corn syrup, fructose and glucose, or high intensity,non-nutritive sweeteners such as aspartame, acesulfame K, sucralose,cyclamate, sodium saccharin, neotame, rebaudioside A, and/or otherstevia-based sweeteners; as well as other optional ingredients such asjuices, organic acids such as citric acid, alcohol and functionalingredients.

Incorporated at levels of 1 ppb to 10 ppm, compounds of formula (I)impart to said beverages containing sweeteners at levels of less than 1%and up to about 20%, an upfront sweetness and mouthfeel that isreminiscent of sugar.

Other preferred edible compositions are savoury compositions, inparticular those that are soy-based or fish-based.

Incorporated at levels of 1 ppb to 10 ppm, in a soy-based composition(such as soy sauce) or a fish-based composition (such as fish sauce)containing 5 to 40% salt, the compositions are found to exhibit strongumami tastes that are long-lasting and rich.

Another preferred edible composition is a clouded beverage composition.

Certain beverages such as juices have relatively higher turbidity andthus have an opaque appearance. Often, it is desired that the beveragehave a relatively high turbidity. This might be desirable to provide amore natural appearance to beverages with low juice content, or it mightbe for reasons related to masking sedimentation or “ringing” (whereflavour or colour oils rise to the surface of a container duringstorage). Clouded beverages are usually formed by means of a cloudingagent. Clouding agents are usually supplied in the form of emulsions, orthe clouding agent may be part of a powdered beverage that uponreconstitution will formed an emulsion providing a permanent cloud tothe beverage.

Compounds of the formula (I), in addition to their remarkableorganoleptic properties, can lend stability to clouding agents and tobeverage compositions containing same.

Accordingly, there is provided in another aspect of the presentdisclosure a composition comprising a beverage clouding composition anda compound of formula (I).

In a particular embodiment of the present disclosure, a flavourcomposition as herein defined may be provided in the form of anemulsion. This emulsion composition may be particularly useful inclouded beverage applications, in particular, in which it is intended toemploy a clouding agent.

In yet another aspect of the present disclosure there is provided aclouded beverage composition comprising a clouding agent and a compoundof the formula (I).

Other preferred edible compositions are those compositions that areformed by a process of ripening.

In food processing, it frequently occurs that a food needs to remain fora prolonged period of time and under well-defined conditions to obtainthe food with the requisite and recognised quality. A commonly used termfor this process is ripening. Ripening is well known in the processingof certain types of cheese, meat, soy-sauce and wine, as well as beersausage, sauerkraut, tempeh and tofu. There are also specific steps thatare carried out for specific reasons (such as water-removal, or off-noteremoval) that have beneficial effects on the food products. Examples ofthis are the conching of chocolate and the drying of noodles, vegetablesand fruits. The transformations that improve the quality of the food areinduced by chemical conversions, enzymatically catalysed conversions orfermentative transformations. All of these conversions are slow andtherefore expensive; they are also not fully predictable orcontrollable.

The compounds of formula (I), having regard to their remarkable propertyof adding to the authentic taste characteristics of the ediblecompositions in which they are incorporated, may be added to an edibleproduct during its ripening process in order to reduce storage timewithout adversely influencing the taste quality of the ripened product.

Accordingly, in another aspect of the present disclosure there isprovided a method of ripening a product selected from the groupconsisting of cheese, meat, soy-sauce and wine, beer, sausage,sauerkraut, tempeh and tofu, comprising the step of ripening the productin the presence of a compound according to the formula (I).

In another aspect of the present disclosure there is provided a methodof conching chocolate, said method comprising the step of adding to thechocolate a compound according to the formula (I), or a flavourcomposition containing same.

There now follows a series of illustrative, non-limiting examples.

SYNTHESIS EXAMPLES 1. General Structure

R¹=is a straight chain hydrocarbon group having 2 to 18 carbon atoms andcontaining zero to three double bonds or

R¹ is a[(1E)-2,6-dimethylhepta-1,5-dien-1-yl]-group.

Several compounds belonging to that general formula have beensynthesized according to one of the 2 procedure described below.

2. Synthesis 2.1 Route A: (Acid Chloride Method) General Procedure forMaking Amide A:

To a solution of methionine sulfoxide (0.6 g, 3.63 mmol) in 1:1 THF: 1NNaOH (20 ml:20 ml) at room temperature was added oleoyl chloride (1.1 g,3.66 mmol) dropwise. The reaction was then stirred at room temperaturefor 7 hours. THF was removed under vacuum. Concentrated HCl was added toadjust the pH to 2. The aqueous layer was then extracted with EtOA_(c)3×and the organic layers were combined. The combined organic layer waswashed with water, brine, dried (Na₂SO₄) and concentrated. The residuewas chromatographed on silica gel (5% MeOH/DCM, 0.1% formic acid) togive 0.56 g (34.1%) of the product as a white solid.

2.2 Route B (DCC Method)

To a solution of (z)-dodec-5-enoic acid (5.04 mmol) with1-hydroxypyrrolidine-2,5-dione (7.56 mmol) in THF (30 ml) was added DCC(7.77 mmol) at 0° C. The mixture was stirred at room temperatureovernight. The formed solids (dicyclohexylurea) were removed byfiltration and the filtrate was added to a solution of2-amino-4-(methylsulfinyl) butanoic acid (6.05 mmol) and potassiumcarbonate (6.08 mmol) in water (30 ml) at room temperature. The mixturewas stirred at room temperature for 7 hours. THF was evaporated undervacuum and the aqueous residue was acidified with conc. HCl to pH of 2.The aqueous layer was then extracted with EtOA_(c)3× and the organiclayers were combined. The combined organic layer was washed with water,brine, dried (Na₂SO₄) and concentrated. The residue was chromatographedon silica gel (5% MeOH/DCM, 0.1% formic acid) to give 0.81 g (36.8%) ofclear oil as product.

2.3 All Synthesized Compounds

TABLE 1 List of synthesized compounds Carboxylic Structure Amino acidacid Structure Route 1 Methionine sulfoxide C2:0

A 2 Methionine sulfoxide C6:0

A 3 Methionine sulfoxide C10:0

A 4 Methionine sulfoxide C12:1

A 5 Methionine sulfoxide C12:0

A 6 Methionine sulfoxide C14:0

A 7 Methionine sulfoxide C15:0

8 Methionine sulfoxide C16:0

9 Methionine sulfoxide C17:0

10 Methionine sulfoxide C18:2

11 Methionine sulfoxide C18:1

12 Methionine sulfoxide C18:0

3 NMR Data (Examples) 3.1 Structure 3 Met-SO C12:1

(2S)-2-((Z)-dodec-5-enamido)-4-(methylsulfinyl)butanoic acid

36.8% yield;

¹H NMR (300 MHz, CD₃OD) δ ppm 0.90 (t, J=7.5 Hz, 3H), 1.24-1.40 (m, 8H),1.61-1.73 (q, J=6.6 Hz, 2H), 2.01-2.17 (m, 5H), 2.27 (t, J=5.7 Hz, 2H),2.30-2.44 (m, 1H), 2.65 (s, 3H), 2.75-2.99 (m, 2H), 4.50-4.58 (m, 1H),5.32-5.45 (m, 2H).

¹³C NMR (300 MHz, CD₃OD) δ ppm 12.94, 22.19, 24.34, 24.49, 25.40, 25.42,26.22, 26.70, 28.55, 29.31, 31.42, 34.87, 36.67, 49.71, 49.77, 50.88,51.13, 128.26, 130.31, 172.58, 174.71, 174.77.

3.2 Structure 5 Met-SO C18:1

(2S)-4-(methylsulfinyl)-2-oleamidobutanoic acid

34.1% yield;

¹H NMR (300 MHz, CD₃OD) δ ppm 0.88 (t, J=8.1 Hz, 3H), 1.28-1.33 (m,20H), 1.56-1.67 (q, J=8.7 Hz, 2H), 2.03-2.17 (m, 5H), 2.25 (t, J=6.3 Hz,2H), 2.31-2.41 (m, 1H), 2.63 (s, 3H), 2.72-2.97 (m, 2H), 4.50-4.57 (m,1H), 5.28-5.39 (m, 2H).

¹³C NMR (300 MHz, CD₃OD) δ ppm 12.96, 22.24, 24.37, 24.45, 25.34, 25.36,26.64, 26.66, 28.76, 28.80, 28.85, 28.87, 28.94, 29.11, 29.35, 31.56,35.34, 36.69, 49.75, 49.83, 50.89, 51.15, 129.32, 129.38, 172.66,174.91, 174.97.

In accordance with another embodiment, the applicant has now found thata S-Methylcysteine sulfoxide connected to a fatty acid residue throughan amide bond may be employed as flavour ingredients that complement oraccentuate the taste and mouthfeel characteristics of ediblecompositions into which they are incorporated across a wide category offlavour applications.

The present disclosure provides in a first aspect compounds of formula(II)

their edible salts, and their use in edible compositions

wherein

R₁ is an alkyl residue containing 2 to 18 carbon atoms, or an alkeneresidue containing from 9 to 25 carbon atoms with 1 to 6 double bonds,R₁ together with the carbonyl group to which it is attached is a residueof a carboxylic acid.

In one embodiment, a compound of the formula (II) is(2S)-3-(methylsulfinyl)-2-oleamidopropanoic acid synthesized accordingto Route A described above and having the structure:

The sulfoxide compounds of formula (II) impart remarkable organolepticproperties to edible compositions to which they are added. Inparticular, they impart highly intense, authentic and harmoniousflavour, and a roundness and fullness to edible compositions containingthem.

More particularly, the compounds can be incorporated into an edibleproduct to impart a remarkable mouthfeel, body and enhanced fatperception; or an enhanced umami or salt taste. They are particularlyuseful in applications low in fat, salt and umami.

This finding was all the more surprising considering that when applicanttasted the compounds in dilute aqueous solution, they were eithertasteless or they exhibited a disappointing, faintly fatty tasteprofile. As such, they appeared to be quite unsuitable for use inflavour applications. Only their combination with flavour co-ingredientsand the judicious selection of their usage levels was it possible todiscover the remarkable organoleptic properties of these compounds.Their effect on edible compositions is quite unusual in that rather thanexerting a characteristic flavour profile to a foodstuff or a beverage,they actually complement, lift or accentuate the essential or authenticflavour and mouth feel characteristics of the foods or beverages inwhich they are incorporated. Accordingly, the compounds of the presentdisclosure find utility in a broad spectrum of applications in the foodand beverage industry, as well as in health and wellness.

Accordingly, in one embodiment, a method of conferring flavour and/ormouthfeel to, or improving taste and/or mouthfeel of an ediblecomposition, which method comprises adding to said composition asulfoxide compound of formula (II) defined herein.

The remarkable organoleptic effects are observed when the sulfoxidecompounds of formula (II) are incorporated into an edible compositioncontaining one or more flavour co-ingredients.

The flavour co-ingredients may be sugars, fats, salt (e.g. sodiumchloride), MSG, calcium ions, phosphate ions, organic acids, proteins,purines and mixtures thereof

Application Examples

Testing with Methionine Sulfoxide Derivatives

Samples were evaluated by expert tasters. Tasters were asked to describethe samples focusing on authentic taste, mouthfeel, fullness,salty-ness, salivation, umami, sweetness, juiciness, richness, longlastingness and fattiness

Comparison in a Cheese Onion Crisp

Base is a crisp with proprietary cheese onion powder flavoring @ 6%

Base plus Met-SO C18:1 at 10 ppb: salt/taste level enhanced; onioncharacter more fried

Comparison in Onion Soup

Base is Campbell's® French onion soup

Base plus Met-SO C18:1 at 10 ppb: slightly stronger in salt; onioncharacter slightly enhanced

Comparison in Onion Soup

Base is UNOX ‘Franse uiensoep’

Base plus Met-SO C18:1 at 10 ppb: slightly stronger in salt; onioncharacter increased

Application Examples

Testing with S-Methylcysteine sulfoxide derivative

Samples were evaluated by expert tasters. Tasters were asked to describethe samples focusing on authentic taste, mouthfeel, fullness,salty-ness, salivation, umami, sweetness, juiciness, richness, longlastingness and fattiness.

Comparison in a Cheese Sauce

Base is a Maggie Saus Base with 0.05 g ethanol

Base plus (2S)-3-(methylsulfinyl)-2-oleamidopropanoic acid at 0.5 ppm:salt/umami/fullness/cheesiness level enhanced.

Samples were evaluated by expert tasters. Tasters were asked to describethe samples focusing on authentic taste, mouthfeel, fullness,salty-ness, salivation, umami, sweetness, juiciness, richness, longlastingness and fattiness.

The dimensions and values disclosed herein are not to be understood asbeing strictly limited to the exact numerical values recited. Instead,unless otherwise specified, each such dimension is intended to mean boththe recited value and a functionally equivalent range surrounding thatvalue. For example, a dimension disclosed as “40 mm” is intended to mean“about 40 mm”.

While particular embodiments have been illustrated and described, itwould be obvious to those skilled in the art that various other changesand modifications can be made without departing from the spirit andscope of the invention. It is therefore intended to cover in theappended claims all such changes and modifications that are within thescope of this invention.

What is claimed is:
 1. A compound of formula (I)

and edible salts thereof, wherein R₁ is an alkyl residue containing 2 to18 carbon atoms, or an alkene residue containing from 9 to 25 carbonatoms with 1 to 6 double bonds, R₁ together with the carbonyl group towhich it is attached is a residue of a carboxylic acid.
 2. The compoundaccording to claim 1 selected from the group consisting of:N-geranoyl-Met, N-palmitoyl-Met, N-palmitenoyl-Met, N-stearoyl-Met,N-linoleoyl-Met and N-linolenoyl-Met.
 3. A stock solution comprising0.01 to 1% by weight of a compound according to formula (I) of claim 1.4. The stock solution according to claim 3 wherein the solvent isselected from the group consisting of: ethanol, triacetine, glycerol,miglyol and mixtures thereof.
 5. An edible composition comprising acompound according to formula (I) of claim
 1. 6. A flavour compositioncomprising a compound according to claim
 1. 7. The flavour compositionaccording to claim 6 comprising at least one flavour co-ingredient. 8.The flavour composition according to claim 6 comprising an ingredientselected from the group consisting of: sugars, fats, salt, MSG, calciumions, phosphate ions, organic acids, proteins, purines and mixturesthereof.
 9. The flavour composition according to claim 6 comprising acarrier material and an adjuvant.
 10. The flavour composition accordingto claim 9, wherein the adjuvant is an anti-oxidant.
 11. The flavourcomposition according to claim 6 in the form of an emulsion.
 12. Theflavour composition according to 6, wherein the flavour composition isin the form of a powder.
 13. The flavour composition according to claim12, wherein the flavour composition is a spray dried powder.
 14. Acompound according to claim 1, selected from the group consisting of(2S)-2-acetamido-4-(methylsulfinyl)butanoic acid;(2S)-2-hexanamido-4-(methylsulfinyl)butanoic acid;(2S)-2-decanamido-4-(methylsulfinyl)butanoic acid;(2S)-2-((Z)-dodec-5-enamido)-4-(methylsulfinyl)butanoic acid;(2S)-2-dodecanamido-4-(methylsulfinyl)butanoic acid;(2S)-4-(methylsulfinyl)-2-tetradecanamidobutanoic acid;(2S)-4-(methylsulfinyl)-2-pentadecanamidobutanoic acid;(2S)-4-(methylsulfinyl)-2-palmitamidobutanoic acid;(2S)-2-heptadecanamido-4-(methylsulfinyl)butanoic acid;(2S)-4-(methylsulfinyl)-2-((9Z,12Z)-octadeca-9,12-dienamido)butanoicacid; (2S)-4-(methylsulfinyl)-2-oleamidobutanoic acid; and(2S)-4-(methylsulfinyl)-2-stearamidobutanoic acid.
 15. A flavourcomposition comprising: a sulfoxide compound selected from the groupconsisting of (2S)-2-acetamido-4-(methylsulfinyl)butanoic acid;(2S)-2-hexanamido-4-(methylsulfinyl)butanoic acid;(2S)-2-decanamido-4-(methylsulfinyl)butanoic acid;(2S)-2-((Z)-dodec-5-enamido)-4-(methylsulfinyl)butanoic acid;(2S)-2-dodecanamido-4-(methylsulfinyl)butanoic acid;(2S)-4-(methylsulfinyl)-2-tetradecanamidobutanoic acid;(2S)-4-(methylsulfinyl)-2-pentadecanamidobutanoic acid;(2S)-4-(methylsulfinyl)-2-palmitamidobutanoic acid;(2S)-2-heptadecanamido-4-(methylsulfinyl)butanoic acid;(2S)-4-(methylsulfinyl)-2-((9Z,12Z)-octadeca-9,12-dienamido)butanoicacid; (2S)-4-(methylsulfinyl)-2-oleamidobutanoic acid; and(2S)-4-(methylsulfinyl)-2-stearamidobutanoic acid; and at least oneflavour co-ingredient
 16. The flavour composition according to claim 15in the form of an emulsion.
 17. The flavour composition according to 15,wherein the flavour composition is in the form of a powder.
 18. Theflavour composition according to claim 17, wherein the flavourcomposition is a spray dried powder.
 19. An edible compositioncomprising (2S)-3-(methylsulfinyl)-2-oleamidopropanoic acid.
 20. Theedible composition according to claim 19 wherein the edible compositionis a cheese sauce.